#------------------------------------------------------------------------------
#$Date: 2025-08-19 17:49:58 +0300 (Tue, 19 Aug 2025) $
#$Revision: 301806 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/23/50/2235044.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/. The original data for this entry
# were provided by IUCr Journals, http://journals.iucr.org/.
#
# The file may be used within the scientific community so long as
# proper attribution is given to the journal article from which the
# data were obtained.
#
data_2235044
loop_
_publ_author_name
'Veranitisagul, Chatchai'
'Wattanathana, Worawat'
'Kaewvilai, Attaphon'
'Duangthongyou, Tanwawan'
'Laobuthee, Apirat'
'Koonsaeng, Nattamon'
_publ_section_title
;
 2-{[(2-Hydroxy-3,5-dimethylbenzyl)(methyl)amino]methyl}-4,6-dimethylphenol
;
_journal_coeditor_code           HB6793
_journal_issue                   6
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o1826
_journal_paper_doi               10.1107/S1600536812022180
_journal_volume                  68
_journal_year                    2012
_chemical_formula_iupac          'C19 H25 N O2'
_chemical_formula_moiety         'C19 H25 N O2'
_chemical_formula_sum            'C19 H25 N O2'
_chemical_formula_weight         299.40
_chemical_name_systematic
;
2-{[(2-Hydroxy-3,5-dimethylbenzyl)(methyl)amino]methyl}-4,6-dimethylphenol
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                95.412(3)
_cell_angle_beta                 96.482(2)
_cell_angle_gamma                94.238(2)
_cell_formula_units_Z            2
_cell_length_a                   5.4598(4)
_cell_length_b                   12.3285(12)
_cell_length_c                   13.0441(13)
_cell_measurement_reflns_used    2370
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      27.17
_cell_measurement_theta_min      3.16
_cell_volume                     865.33(14)
_computing_cell_refinement       'XSCANS (Siemens, 1992)'
_computing_data_collection       'XSCANS (Siemens, 1992)'
_computing_data_reduction        'XSCANS (Siemens, 1992)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.990
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measurement_device_type  'Siemens P4'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0205
_diffrn_reflns_av_sigmaI/netI    0.0340
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            6613
_diffrn_reflns_theta_full        27.56
_diffrn_reflns_theta_max         27.56
_diffrn_reflns_theta_min         1.58
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 3
_diffrn_standards_interval_time  120
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.074
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.149
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             324
_exptl_crystal_size_max          0.52
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.24
_refine_diff_density_max         0.265
_refine_diff_density_min         -0.257
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.060
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     299
_refine_ls_number_reflns         3944
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.060
_refine_ls_R_factor_all          0.0755
_refine_ls_R_factor_gt           0.0495
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.1149P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1492
_refine_ls_wR_factor_ref         0.1822
_reflns_number_gt                2722
_reflns_number_total             3944
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            hb6793.cif
_cod_data_source_block           I
_cod_database_code               2235044
_cod_database_fobs_code          2235044
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_occupancy
_atom_site_symmetry_multiplicity
O O1 0.5039(2) 0.38818(10) 0.16018(10) 0.0517(3) Uani d 1 1
N N 0.2371(2) 0.21998(11) 0.04228(10) 0.0404(3) Uani d 1 1
C C1 0.4085(3) 0.34523(12) 0.24228(13) 0.0427(4) Uani d 1 1
C C14 0.4502(3) 0.30149(13) -0.15535(12) 0.0428(4) Uani d 1 1
C C10 0.3116(4) 0.11247(15) -0.20468(13) 0.0532(4) Uani d 1 1
C C2 0.5258(3) 0.37697(14) 0.34231(14) 0.0479(4) Uani d 1 1
C C6 0.1937(3) 0.27292(13) 0.22555(12) 0.0423(4) Uani d 1 1
C C9 0.2935(3) 0.20900(14) -0.14369(12) 0.0435(4) Uani d 1 1
C C3 0.4254(3) 0.33434(15) 0.42452(14) 0.0529(4) Uani d 1 1
C C7 0.0629(3) 0.24498(16) 0.11772(13) 0.0487(4) Uani d 1 1
C C5 0.1029(3) 0.23192(15) 0.31059(14) 0.0496(4) Uani d 1 1
C C13 0.6237(3) 0.29546(15) -0.22569(14) 0.0490(4) Uani d 1 1
C C8 0.1141(3) 0.21588(16) -0.06464(13) 0.0472(4) Uani d 1 1
C C11 0.4815(4) 0.10371(16) -0.27587(14) 0.0571(5) Uani d 1 1
C C4 0.2141(3) 0.26180(15) 0.41101(14) 0.0529(4) Uani d 1 1
C C12 0.6338(4) 0.19581(17) -0.28429(14) 0.0556(5) Uani d 1 1
C C19 0.3486(4) 0.11876(15) 0.06030(16) 0.0532(4) Uani d 1 1
C C16 0.1053(6) 0.2193(3) 0.50252(19) 0.0796(7) Uani d 1 1
C C15 0.7506(4) 0.45821(19) 0.3588(2) 0.0640(5) Uani d 1 1
C C18 0.7977(4) 0.3916(2) -0.2386(2) 0.0651(6) Uani d 1 1
C C17 0.4954(9) -0.0025(2) -0.3427(2) 0.0933(9) Uani d 1 1
O O2 0.4257(2) 0.39465(10) -0.09216(10) 0.0585(4) Uani d 1 1
H H5 -0.048(3) 0.1827(16) 0.2992(14) 0.052(5) Uiso d 1 1
H H12 0.751(4) 0.1965(19) -0.3286(19) 0.079(7) Uiso d 1 1
H H7B -0.068(4) 0.1831(17) 0.1203(15) 0.061(5) Uiso d 1 1
H H10 0.205(4) 0.0478(19) -0.1977(17) 0.067(6) Uiso d 1 1
H H3 0.510(4) 0.353(2) 0.497(2) 0.083(7) Uiso d 1 1
H H19C 0.222(4) 0.0535(19) 0.0524(17) 0.073(6) Uiso d 1 1
H H8B -0.017(4) 0.1503(18) -0.0811(16) 0.066(6) Uiso d 1 1
H H8A 0.020(3) 0.2867(16) -0.0664(15) 0.056(5) Uiso d 1 1
H H19B 0.430(4) 0.1259(18) 0.1319(19) 0.069(6) Uiso d 1 1
H H16A -0.068(8) 0.216(4) 0.490(3) 0.167(16) Uiso d 1 1
H H19A 0.466(4) 0.1081(18) 0.0130(17) 0.069(6) Uiso d 1 1
H H18B 0.855(4) 0.4335(17) -0.1729(18) 0.059(6) Uiso d 1 1
H H7A -0.030(4) 0.3078(17) 0.0938(15) 0.060(5) Uiso d 1 1
H H17A 0.644(8) -0.001(4) -0.363(4) 0.155(17) Uiso d 1 1
H H18A 0.944(5) 0.369(2) -0.257(2) 0.091(8) Uiso d 1 1
H H15B 0.827(5) 0.459(2) 0.433(3) 0.110(9) Uiso d 1 1
H H15C 0.718(4) 0.535(2) 0.335(2) 0.088(7) Uiso d 1 1
H H' 0.426(5) 0.331(2) 0.100(2) 0.097(8) Uiso d 1 1
H H16C 0.188(6) 0.241(3) 0.565(3) 0.142(13) Uiso d 1 1
H H18C 0.729(4) 0.443(2) -0.276(2) 0.086(7) Uiso d 1 1
H H'' 0.483(5) 0.457(3) -0.122(2) 0.104(9) Uiso d 1 1
H H16B 0.079(7) 0.133(4) 0.490(3) 0.139(12) Uiso d 1 1
H H17C 0.424(9) 0.000(4) -0.409(5) 0.184(18) Uiso d 1 1
H H15A 0.879(5) 0.432(2) 0.327(2) 0.086(8) Uiso d 1 1
H H17B 0.490(6) -0.064(3) -0.304(3) 0.136(12) Uiso d 1 1
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_publ_flag
C1 O1 H' 100.4(15) ?
C19 N C7 111.00(14) n
C19 N C8 111.41(14) n
C7 N C8 110.75(12) n
O1 C1 C2 118.74(14) n
O1 C1 C6 120.42(15) n
C2 C1 C6 120.82(14) n
O2 C14 C13 123.18(14) n
O2 C14 C9 116.30(14) n
C13 C14 C9 120.50(16) n
C9 C10 C11 122.18(17) n
C9 C10 H10 120.0(13) ?
C11 C10 H10 117.8(13) ?
C3 C2 C1 118.13(15) n
C3 C2 C15 121.91(17) n
C1 C2 C15 119.93(17) n
C5 C6 C1 118.57(15) n
C5 C6 C7 121.62(14) n
C1 C6 C7 119.77(14) n
C10 C9 C14 118.83(15) n
C10 C9 C8 121.39(15) n
C14 C9 C8 119.77(15) n
C2 C3 C4 122.74(17) n
C2 C3 H3 119.9(13) ?
C4 C3 H3 117.3(13) ?
N C7 C6 111.73(13) n
N C7 H7B 113.6(11) n
C6 C7 H7B 107.5(12) ?
N C7 H7A 107.2(11) ?
C6 C7 H7A 111.3(11) ?
H7B C7 H7A 105.5(16) ?
C4 C5 C6 122.20(16) n
C4 C5 H5 119.1(11) ?
C6 C5 H5 118.7(11) ?
C14 C13 C12 117.91(15) n
C14 C13 C18 122.03(18) n
C12 C13 C18 120.06(17) n
N C8 C9 112.46(12) n
N C8 H8B 110.9(11) ?
C9 C8 H8B 108.7(11) ?
N C8 H8A 105.3(11) ?
C9 C8 H8A 112.1(10) ?
H8B C8 H8A 107.3(15) ?
C12 C11 C10 117.31(17) n
C12 C11 C17 121.5(2) n
C10 C11 C17 121.2(2) n
C5 C4 C3 117.52(16) n
C5 C4 C16 121.06(19) n
C3 C4 C16 121.40(19) n
C11 C12 C13 123.26(16) n
C11 C12 H12 122.7(15) ?
C13 C12 H12 114.1(15) ?
N C19 H19C 112.4(12) ?
N C19 H19B 108.3(13) ?
H19C C19 H19B 107.1(18) ?
N C19 H19A 108.2(13) ?
H19C C19 H19A 110.3(18) ?
H19B C19 H19A 110.5(18) ?
C4 C16 H16A 109(3) ?
C4 C16 H16C 116(2) ?
H16A C16 H16C 123(3) ?
C4 C16 H16B 109(2) ?
H16A C16 H16B 84(3) ?
H16C C16 H16B 111(3) ?
C2 C15 H15B 107.5(17) ?
C2 C15 H15C 114.4(13) ?
H15B C15 H15C 116(2) ?
C2 C15 H15A 111.8(16) ?
H15B C15 H15A 98(2) ?
H15C C15 H15A 109(2) ?
C13 C18 H18B 111.5(12) ?
C13 C18 H18A 110.3(17) ?
H18B C18 H18A 101(2) ?
C13 C18 H18C 114.8(15) ?
H18B C18 H18C 102(2) ?
H18A C18 H18C 116(2) ?
C11 C17 H17A 107(3) ?
C11 C17 H17C 111(3) ?
H17A C17 H17C 91(3) ?
C11 C17 H17B 112(2) ?
H17A C17 H17B 104(4) ?
H17C C17 H17B 127(4) ?
C14 O2 H'' 110.3(18) ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
O1 C1 1.3750(19) n
O1 H' 1.04(3) n
N C19 1.456(2) n
N C7 1.472(2) n
N C8 1.473(2) n
C1 C2 1.394(2) n
C1 C6 1.403(2) n
C14 O2 1.373(2) n
C14 C13 1.392(2) n
C14 C9 1.405(2) n
C10 C9 1.384(2) n
C10 C11 1.387(3) n
C10 H10 0.97(2) ?
C2 C3 1.387(3) n
C2 C15 1.508(3) n
C6 C5 1.387(2) n
C6 C7 1.501(2) n
C9 C8 1.501(2) n
C3 C4 1.391(3) n
C3 H3 1.00(3) ?
C7 H7B 1.01(2) ?
C7 H7A 1.01(2) ?
C5 C4 1.384(3) n
C5 H5 0.973(18) ?
C13 C12 1.393(3) n
C13 C18 1.498(3) n
C8 H8B 1.03(2) ?
C8 H8A 1.05(2) ?
C11 C12 1.378(3) n
C11 C17 1.515(3) n
C4 C16 1.511(3) n
C12 H12 0.91(2) ?
C19 H19C 1.01(2) ?
C19 H19B 0.98(2) ?
C19 H19A 0.94(2) ?
C16 H16A 0.94(4) ?
C16 H16C 0.89(4) ?
C16 H16B 1.05(4) ?
C15 H15B 1.01(3) ?
C15 H15C 1.05(3) ?
C15 H15A 0.92(3) ?
C18 H18B 0.96(2) ?
C18 H18A 0.92(3) ?
C18 H18C 0.91(3) ?
C17 H17A 0.88(4) ?
C17 H17C 0.91(6) ?
C17 H17B 0.96(4) ?
O2 H'' 0.95(3) n
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
O1 H' N . 1.03(3) 1.71(3) 2.6895(18) 156(2)
O2 H'' O1 2_665 0.94(3) 2.02(4) 2.9114(18) 158(2)
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
O1 C1 C2 C3 179.02(15)
C6 C1 C2 C3 0.6(2)
O1 C1 C2 C15 0.9(2)
C6 C1 C2 C15 -177.59(17)
O1 C1 C6 C5 -179.66(14)
C2 C1 C6 C5 -1.2(2)
O1 C1 C6 C7 -1.9(2)
C2 C1 C6 C7 176.55(15)
C11 C10 C9 C14 0.9(3)
C11 C10 C9 C8 -177.98(17)
O2 C14 C9 C10 -179.40(15)
C13 C14 C9 C10 -1.2(2)
O2 C14 C9 C8 -0.5(2)
C13 C14 C9 C8 177.70(14)
C1 C2 C3 C4 0.0(3)
C15 C2 C3 C4 178.09(18)
C19 N C7 C6 67.71(18)
C8 N C7 C6 -167.98(14)
C5 C6 C7 N -136.72(16)
C1 C6 C7 N 45.6(2)
C1 C6 C5 C4 1.4(3)
C7 C6 C5 C4 -176.34(16)
O2 C14 C13 C12 178.87(15)
C9 C14 C13 C12 0.8(2)
O2 C14 C13 C18 -0.5(3)
C9 C14 C13 C18 -178.61(17)
C19 N C8 C9 -65.34(18)
C7 N C8 C9 170.58(14)
C10 C9 C8 N 105.66(17)
C14 C9 C8 N -73.2(2)
C9 C10 C11 C12 -0.2(3)
C9 C10 C11 C17 -179.2(2)
C6 C5 C4 C3 -0.9(3)
C6 C5 C4 C16 177.5(2)
C2 C3 C4 C5 0.2(3)
C2 C3 C4 C16 -178.2(2)
C10 C11 C12 C13 -0.3(3)
C17 C11 C12 C13 178.8(2)
C14 C13 C12 C11 0.0(3)
C18 C13 C12 C11 179.35(19)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 24785914
2 PubChem 12132593
